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Top cities in Frederick County

A white neoclassical building with columns, an American flag, and a clock tower.
Vacation Rentals

Winchester

Winchester

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Frederick County holiday rentals

A modern living room with a sofa, a coffee table, and a lamp. There is a kitchen area in the background with cabinets and a painting on the wall.

1. Executive Suites

Executive Suites
3.0 star property
Winchester
The price is £177
includes taxes & fees
18 Nov - 19 Nov
Executive Suites
A hallway with a wooden staircase, a hanging light fixture, and a welcome mat.

2. Rosamond nice downtown studio apt

Rosamond nice downtown studio apt
Winchester Historic District
8.8 out of 10, Excellent, (3 reviews)
"Easy space for a 2 person weekend getaway, very close within walking distance to food, shops, breweries, etc"
United States
Jameson D.
The price is £139
includes taxes & fees
12 Nov - 13 Nov
Rosamond nice downtown studio apt
A modern kitchen with stainless steel appliances, white cabinetry, and a central island.

3. The Queen of Winchester Three Bedroom with Upper Level Deck

The Queen of Winchester Three Bedroom with Upper Level Deck
Winchester
7.6 out of 10, Good, (8 reviews)
"If you want to be in the town and have quick access to everything, this is the place for you."
United States
Chris C.
The price is £180
includes taxes & fees
29 Nov - 30 Nov
The Queen of Winchester Three Bedroom with Upper Level Deck
A hot tub in front of a wooden cabin with a tree in the background.

4. Luxury tiny home farm stay on historic property with hot tub in Stephens City

Luxury tiny home farm stay on historic property with hot tub in Stephens City
Stephens City
10.0 out of 10, Exceptional, (15 reviews)
"This tiny house was an absolute dream to stay at! Jen is very attentive to detail- everything from the decor to the thoughtful welcome basket and supplying a feed bucket for the farm animals was perfection. My kids requested our next vacation just be there instead! "
United States
Laura H.
The price is £132
includes taxes & fees
16 Nov - 17 Nov
Luxury tiny home farm stay on historic property with hot tub in Stephens City
A living room with a blue sofa, a wooden coffee table, a white armchair, and a dining area with a mirror and flowers.

5. Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Winchester Historic District
8.4 out of 10, Very good, (6 reviews)
"Loved being so close to the old town; was able to walk to a lot of places. Great to have an assigned parking spot in a lot behind the building. Enjoyed staying here a lot!"
United States
Leslie L.
The price is £170
includes taxes & fees
17 Nov - 18 Nov
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
A living room with a glass-top coffee table, wicker chairs, a sofa, and a painting on the wall.

6. Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!

Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Winchester Historic District
8.8 out of 10, Excellent, (5 reviews)
"The unit is very nice, exactly as described, The bed are comfortable and everything was fine. The location is excellent very near to historical sights and downtown shopping district."
United States
Timothy B.
The price is £188
includes taxes & fees
19 Nov - 20 Nov
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
A compact kitchen with a central island, wooden cabinets, a microwave, and a refrigerator.

7. Buena Vista

Buena Vista
Shawneeland
10.0 out of 10, Exceptional, (1 review)
The price is £142
includes taxes & fees
9 Dec - 10 Dec
Buena Vista
A building with a red door, white trim, and a small balcony with a metal railing.

8. The Stock Exchange downtown 3rd floor studio apt

The Stock Exchange downtown 3rd floor studio apt
Winchester Historic District
7.0 out of 10, Good, (2 reviews)
"Everything went smoothly. Easy stay. Clean. Small efficiency with futon for bed."
United States
Greg A.
The price is £137
includes taxes & fees
15 Nov - 16 Nov
The Stock Exchange downtown 3rd floor studio apt
A living room with a sofa, ottoman, lamp, and a mirror.

9. Morocco Loft 2BR overlooking city walking mall

Morocco Loft 2BR overlooking city walking mall
Old Town Winchester
10.0 out of 10, Exceptional, (3 reviews)
"Great property with all the comforts of home"
United States
Kristen R.
The price is £217
includes taxes & fees
11 Nov - 12 Nov
Morocco Loft 2BR overlooking city walking mall
A two-story house with a front porch, a mailbox, and a number plate.

10. Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.8 out of 10, Exceptional, (11 reviews)
"The property was exceptional and very comfortable. We enjoyed the amenities. We would book it for future trips again."
United States
Carolyn F.
The price is £251
includes taxes & fees
11 Nov - 12 Nov
Cameron Charmer pristine downtown apt with double master suites
A living room with a sofa, armchair, coffee table, and a television.

11. Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
9.0 out of 10, Wonderful, (22 reviews)
"Easy access to nearby attractions. Convenient to all we hoped to see and do while we were here."
United States
Melissa J.
The price is £229
includes taxes & fees
15 Nov - 16 Nov
Nostalgia Lane in the heart of the city
A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.

12. ❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (88 reviews)
"Great little getaway. Our only issue was the intense heat of 100 every day. The AC was heavenly!"
United States
Dennis C.
The price is £78
includes taxes & fees
17 Nov - 18 Nov
❤️ Secluded 1940s Romantic Tiny House on the River
A room with a large window, a round table, and two chairs.

13. Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!

Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!
Harpers Ferry
10.0 out of 10, Exceptional, (112 reviews)
"Absolutely charming cabin - clean, comfortable and with lovely amenities."
United States
Diane S.
The price is £225
includes taxes & fees
1 Dec - 2 Dec
Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!
A cabin with a porch, wooden steps, and a small table and chair.

14. Mountain Retreat w/ Loft, Fire Pit, & Grill

Mountain Retreat w/ Loft, Fire Pit, & Grill
Delray
9.2 out of 10, Wonderful, (12 reviews)
"Clean and as advertised. Gravel road was fine for most vehicles as long as they have a little clearance"
United States
Rex W.
The price is £152
includes taxes & fees
11 Nov - 12 Nov
Mountain Retreat w/ Loft, Fire Pit, & Grill
A wooden deck with white railings and a covered porch area.

15. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (51 reviews)
"Very cute and clean home. The location was great and Vanessa was awesome to work with"
United States
Diedra
The price is £160
includes taxes & fees
22 Nov - 23 Nov
Mountain View Bungalow in Front Royal
A living room with a dining table, chairs, a sofa, and a television.

16. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (27 reviews)
"Absolutely adorable, perfect location and well appointed. Would absolutely stay here again. Highly recommend and maybe if you’re lucky you’ll meet the little black cat who visited us!!"
United States
Abigail
The price is £157
includes taxes & fees
15 Nov - 16 Nov
Quaint Mini Cottage in Shepherdstown - Walking Distance
A two-story house with a balcony, surrounded by trees and snow.

17. Cozy A frame cabin in quaint Front Royal. Dog friendly

Cozy A frame cabin in quaint Front Royal. Dog friendly
Front Royal
9.4 out of 10, Exceptional, (11 reviews)
"Had a good time during my stay and loved seeing Shenandoah"
United States
Kye Y.
The price is £202
includes taxes & fees
11 Nov - 12 Nov
Cozy A frame cabin in quaint Front Royal. Dog friendly
A spacious living room with a fireplace, a dining area with a bench, and a large sliding glass door leading to an outdoor patio.

18. The Honeymoon Cabin | Private Couple's Retreat w/ hot tub

The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
Front Royal
9.6 out of 10, Exceptional, (9 reviews)
"Great little hideout! We loved this little place, accurately described and the communication was superb!"
United States
P H.
The price is £278
includes taxes & fees
16 Nov - 17 Nov
The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
A hotel entrance with a sign, a wicker chair, a wooden lattice, and a white door.

19. Best location! The Pullman Apt @ historic 1799 Inn

Best location! The Pullman Apt @ historic 1799 Inn
Harpers Ferry
9.2 out of 10, Wonderful, (62 reviews)
"Location is unbeatable- but bring ear plugs for the train whistling through the night."
United States
Karla
The price is £166
includes taxes & fees
15 Nov - 16 Nov
Best location! The Pullman Apt @ historic 1799 Inn
A hot tub with a view of a forest and a sunset.

20. A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
Linden
9.6 out of 10, Exceptional, (14 reviews)
"Great place to stay to catch the northern entrance to Shenandoah. Comfortable beds, great furniture, and easy drive to Front Royal for dining. "
United States
Scott M.
The price is £240
includes taxes & fees
17 Nov - 18 Nov
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Frederick County Hotel Reviews

A two-story house with a front porch, American flags, and a mailbox.
The Carriage Inn B&B

The Carriage Inn B&B

The Carriage Inn B&B
Charles Town

10/10 Excellent

Lovely introduction to the history of the inn and its connections with the Civil War. Tasty home cooked breakfast including French Apple toast.
United Kingdom
Judith
Reviewed May 22, 2016
The Carriage Inn B&B

Find out more about Frederick County

Everything you need to know about Frederick County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Frederick County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Frederick County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Frederick County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Frederick County. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Frederick County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Frederick County holiday rentals we have selected for you start as low as £77 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Frederick County rentals

At Expedia, we put the best Frederick County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Frederick County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Frederick County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Frederick County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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